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Random article Venlafaxine (also called Effexor or Efexor) is 1 : 1 mixture (racemate)
Donate to Wikipedia an antidepressant of the serotonin-
norepinephrine reuptake inhibitor (SNRI)
Interaction
class. [2][3][4] First introduced by Wyeth in
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1993, now marketed by Pfizer, it is licensed
About Wikipedia
for the treatment of major depressive disorder
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(MDD), as a treatment for generalized anxiety
Recent changes
disorder, and comorbid indications in certain
Contact Wikipedia
anxiety disorders with depression. In 2007,
Toolbox venlafaxine was the sixth most commonly
prescribed antidepressant on the U.S. retail
Print/export
market, with 17.2 million prescriptions. [5] In
Languages children and adolescents, venlafaxine, like
Deutsch other antidepressants, has a potential to
Español increase suicidal thoughts, attempts and
Français events of self-harm. [citation needed]
한국어
Italiano Contents [hide]
Systematic (IUPAC) name
Magyar 1 Indications
(RS)-1-[2-dimethylamino-1-(4-methoxyphenyl)-
Nederlands 1.1 Approved
ethyl]cyclohexanol
Polski 1.1.1 Depression
Identifiers
Português 1.2 Off-label/investigational uses
CAS number 93413-69-5
Русский 2 Contraindications
2.1 Glaucoma ATC code N06AX16
Suomi
2.2 Pregnant women PubChem CID 5656
Svenska
2.3 Heart disease and hypertension DrugBank APRD00125
3 Adverse effects ChemSpider 5454  
3.1 Suicide UNII GRZ5RCB1QG 
3.2 Common side effects Chemical data
3.3 Less common to rare side effects Formula C17 H27 NO 2  
3.4 Dose dependency of adverse events Mol. mass 277.402 g/mol
3.5 Memory loss SMILES eMolecules & PubChem
3.6 Discontinuation syndrome
InChI
3.7 Serotonin syndrome InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-
3.8 Combined serotonin toxicity and SSRI 17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-
discontinuation syndrome (SSRI 3H3  
withdrawal) Key: PNVNVHUZROJLTJ-UHFFFAOYSA-N 
Pharmacokinetic data

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4 Available forms
4.1 Venlafaxine extended release (XR) Bioavailability 10-45% [1 ]
4.2 Generic Protein 27%
5 Overdose binding
5.1 Management of overdose Metabolism Hepatic
6 Mechanism of action Half-life 4.9 ± 2.4 h (parent compound); [1 ] 10.3 ± 4.3
6.1 Pharmacokinetics h (active metabolite) [1 ]
7 Drug interactions Excretion Renal
8 Physical/chemical properties Therapeutic considerations
9 See also Pregnancy C
10 References cat.
11 External links Legal status POM (UK) -only (US)
11.1 Patient experiences Routes Oral
  (what is this?)  (verify)

Indications [edit]

Approved [edit]

Venlafaxine is used primarily for the treatment of major depression in adults. [6]

Depression [edit]

Multiple double blind studies show venlafaxine's effectiveness in treating depression. Venlafaxine has
similar efficacy to the tricyclic antidepressants amitriptyline (Elavil) and imipramine, and is better
tolerated than amitriptyline. Its efficacy is similar to or better than sertraline (Zoloft) and fluoxetine
(Prozac), depending on the criteria and rating scales used. Higher doses of venlafaxine are more
effective, and more patients achieved remission or were "very much improved". The efficacy was
similar if the number of patients who achieved "response" or were "improved" was considered. A
meta-analysis comparing venlafaxine and combined groups of SSRI or tricyclic antidepressants
showed venlafaxine's superiority. [7] Judged by the same criteria, venlafaxine was similar in efficacy to
the atypical antidepressant bupropion (Wellbutrin); however, the remission rate was significantly
lower for venlafaxine. [8] In a double-blind study, patients who did not respond to an SSRI were
switched to venlafaxine or citalopram. Similar improvement was observed in both groups. [9]

Off-label/investigational uses [edit]

Many doctors are starting to prescribe venlafaxine "off label" for the treatment of diabetic neuropathy
(in a similar manner to duloxetine) and migraine prophylaxis (in some people, however, venlafaxine
can exacerbate or cause migraines). Studies have shown venlafaxine's effectiveness for these
conditions. [10][11] It has also been found to reduce the severity of 'hot flashes' in menopausal
women. [12][13]
Substantial weight loss in patients with major depression, generalized anxiety disorder, and social
phobia has been noted, but the manufacturer does not recommend use as an anorectic either alone
or in combination with phentermine or other amphetamine-like drugs. [6] Venlafaxine hydrochloride is
in the phenethylamine class of modern chemicals, which includes amphetamine,
methylenedioxymethamphetamine (MDMA), and methamphetamine. This chemical structure likely
lends to its activating properties; however, some patients find venlafaxine highly sedating, despite its
more common stimulatory effects.
Venlafaxine is not approved for the treatment of depressive phases of bipolar disorder; this has some
potential danger as venlafaxine can induce mania, mixed states, rapid cycling and/or psychosis in
some bipolar patients, particularly if they are not also being treated with a mood stabilizer.[6]
Due to its action on both the serotoninergic and adrenergic systems, venlafaxine is also used as a

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treatment to reduce episodes of cataplexy, a form of muscle weakness, in patients with the sleep
disorder narcolepsy.[14]
Venlafaxine was found in one study to be equal to anafranil (Clomipramine) in the treatment of OCD
with fewer side effects.[15]
Due to its tendency to increase blood pressure and its modulative effects on the autonomic nervous
system, venlafaxine is often used to treat orthostatic intolerance and postural orthostatic tachycardia
syndrome.[16]

Contraindications [edit]

Venlafaxine is contraindicated in children and adolescents because it can increase suicidal thoughts,
attempts, and self-harm (see Venlafaxine#Suicide). Furthermore, studies of venlafaxine in these age
groups have not established its efficacy or safety. [17] Venlafaxine is not recommended in patients
hypersensitive to it, nor should it be taken by anyone who is allergic to the inactive ingredients, which
include gelatin, cellulose, ethylcellulose, iron oxide, titanium dioxide and hypromellose. It should
never be used with a monoamine oxidase inhibitor (MAOI), as it can cause potentially deadly
serotonin syndrome. At least 14 days must pass between the use of venlafaxine and MAO inhibitors.
Caution should also be used in those with a seizure disorder.

Glaucoma [edit]

Venlafaxine can increase eye pressure, so those with glaucoma may require more frequent eye
checks. [6]

Pregnant women [edit]

There are few, well-controlled studies of venlafaxine in pregnant women. A study released in May
2010 by the Canadian Medical Association Journal suggests use of venlafaxine doubles the risk of
miscarriage.[18] Consequently, venlafaxine should only be used during pregnancy if clearly
needed.[6] Prospective studies have not shown any statistically significant congenital
malformations.[19] There have, however, been some reports of self-limiting effects on newborn
infants.[20] As with other serotonin reuptake inhibitors, these effects are generally short-lived, lasting
only 3 to 5 days, [21] and rarely resulting in severe complications. [22] Use of Venlafaxine in
pregnancy should be considered on a case-by-case basis. Venlafaxine use during pregnancy
increases the risk of spontaneous abortion.[23][24]

Heart disease and hypertension [edit]

The FDA asked the manufacturers of all SNRIs to include the risk of persistent pulmonary
hypertension (PPHN) in prescribing data as of July 19, 2006. Medications containing venlafaxine
caused a mean heart rate increase of 4 bpm in clinical trials, along with a sustained increase in
blood pressure in some.

Adverse effects [edit]

Suicide [edit]

The US Food and Drug Administration body (FDA) requires all antidepressants, including venlafaxine,
to carry a black box warning with a generic warning about a possible suicide risk. In addition, the
most recent research [citation needed] indicated that patients taking venlafaxine are at increased risk of
suicide.
A study conducted in Finland followed more than 15,000 patients for 3.4 years. Venlafaxine increased
suicide risk 1.6-fold (statistically significant), as compared to no treatment. At the same time,

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fluoxetine (Prozac) halved the suicide risk.[25]

In another study, the data on more than 200,000 cases were obtained from the UK general practice
research database. The patients taking venlafaxine had significantly higher risk of completed suicide
than the ones on fluoxetine (Prozac) (2.8 times) or citalopram (Celexa) (2.4 times). Even after taking
into consideration the fact that venlafaxine was generally prescribed for more severe depression,
venlafaxine was associated with 1.6-1.7 times more suicides than fluoxetine or citalopram. This
difference was no longer statistically significant due to the rarity of completed suicides. However, for
the attempted suicides (more frequent event) the 1.2-1.3 times higher risk for venlafaxine still stayed
statistically significant after the adjustment. [26]
An analysis of clinical trials by the FDA statisticians showed the incidence of suicidal behaviour
among the adults on venlafaxine to be not significantly different from fluoxetine or placebo. [27] A
possible explanation for this discrepancy is that suicidal patients are generally excluded from clinical
trials, and so clinical trials do not represent the real population of patients. [citation needed]
Venlafaxine is contraindicated in children, adolescents and young adults. According to the FDA
analysis of clinical trials [27] venlafaxine caused a statistically significant 5-fold increase in suicidal
ideation and behavior in persons younger than 25. In another analysis, venlafaxine was no better
than placebo among children (7–11 years old), but improved depression in adolescents (12–17 years
old). However, in both groups, hostility and suicidal behavior increased in comparison to those
receiving a placebo. [28] In a study involving antidepressants that had failed to produce results in
depressed teenagers, teens whose SSRI treatment had failed who were randomly switched to either
another SSRI or to venlafaxine showed an increased rate of suicide on venlafaxine. Among
teenagers who were suicidal at the beginning of the study, the rate of suicidal attempts and self-harm
was significantly higher, by about 60%, after the switch to venlafaxine than after the switch to an
SSRI.[29]

Common side effects [edit]

NOTE: The percentage of occurrences for each side effect listed comes from clinical trial data
provided by Wyeth Pharmaceuticals Inc. The percentages indicate the percentage of people that
experienced the side effect in clinical trials. [6]
Headache (34%)
Nausea (21-35%)
Insomnia (15-23%)
Sexual dysfunction (14-34%)
Dry mouth (12-16%)
Dizziness (11-20%)
Sweating (10-14%)
Decreased appetite (8-20%)
Abnormal ejaculation (8-16%)
Hypertension (4-5%)
Vivid/abnormal dreams (3-7%)
Decreased libido (3-9%)
Increased yawning (3-5%)
Constipation
Fatigue
Vertigo
Anxiety

Less common to rare side effects [edit]

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Note 'Rare' adverse effects occur in fewer than 1 in 1000 patients.

Cardiac arrhythmia
Increased serum cholesterol
Gas or stomach pain
Abnormal vision
Nervousness, agitation or increased anxiety
Panic attacks
Hives
Depressed feelings
Suicidal thoughts
Confusion
Neuroleptic malignant syndrome
Tremor
Drowsiness
Allergic skin reactions
External bleeding
Serious bone marrow damage (thrombocytopenia, agranulocytosis)
Hepatitis
Pancreatitis
Seizure
Tardive dyskinesia
Dysphagia (difficulty swallowing)
Psychosis
Hair loss
Hostility
Activation of mania/hypomania
Weight loss (of concern when treating patients suffering from anorexia nervosa)
Weight gain (effect not clear, but of concern when treating people who may have body
dysmorphic disorder).
Homicidal thoughts
Aggression
Depersonalization
Visual hallucinations
Swollen and/or bleeding gums
Frequent urination

Dose dependency of adverse events [edit]

A comparison of adverse event rates in a fixed-dose study comparing venlafaxine 75, 225, and
375 mg/day with placebo revealed a dose dependency for some of the more common adverse events
associated with venlafaxine use. The rule for including events was to enumerate those that occurred
at an incidence of 5% or more for at least one of the venlafaxine groups and for which the incidence
was at least twice the placebo incidence for at least one venlafaxine group. Tests for potential dose
relationships for these events (Cochran-Armitage test, with a criterion of exact 2-sided p-value
<=0.05) suggested a dose-dependency for several adverse events in this list, including chills,
hypertension, anorexia, nausea, agitation, dizziness, somnolence, tremor, yawning, sweating, and
abnormal ejaculation.[6]

Memory loss [edit]

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In a study of 70 patients that compared the tolerability of venlafaxine at standard doses, ranging from
75 to 300 mg, against relatively high doses (rarely prescribed), ranging from 375 to 600 mg per day,
for treating DSM-IV major depressive disorder, "failing memory" was reported in 44% of cases. The
severity of venlafaxine-induced memory loss was also noted to increase with dose and length of
treatment. [30]

Discontinuation syndrome [edit]

Main article: SSRI discontinuation syndrome
In vitro studies revealed venlafaxine has virtually no affinity for opiate, benzodiazepine, or N-methyl-
D-aspartic acid (NMDA) receptors. It has no significant CNS stimulant activity in rodents. In primate
drug discrimination studies, venlafaxine showed no significant stimulant or depressant abuse
liability.[6]
Many patients stopping venlafaxine use experience SSRI discontinuation syndrome, i.e. withdrawal
symptoms. This is especially noted if a patient misses a dose, but can also occur when reduction of
dosage is gradual. The high risk of discontinuation syndrome symptoms may reflect venlafaxine's
short half-life. [31] Missing even a single dose can induce discontinuation effects in some patients. [32]
Discontinuation is similar in nature to those of SSRIs such as paroxetine (Paxil or Seroxat). Sudden
discontinuation of venlafaxine particularly seemed to cause discontinuation symptoms during the first
3 days in a study of 18 patients. [33] As reported in 2001 by Haddad in the journal Drug Safety,
"another strategy to consider is switching to fluoxetine, which may suppress the discontinuation
symptoms, but which has little tendency to cause such symptoms itself," and then discontinuing
that. [31] Some psychiatrists actually prescribe the singular SSRIs to alleviate the symptoms of
venlafaxine withdrawal.
Although many other drugs can cause withdrawal symptoms which are not associated with addiction
or dependence, for example, anticonvulsants, beta-blockers, nitrates, diuretics, centrally acting
antihypertensives, sympathomimetics, heparin, tamoxifen, dopaminergic agents, antipsychotics, and
lithium,[31] addiction or dependence is a more common effect described for drugs that (are thought
to, or may) improve mental well-being. [34]

Serotonin syndrome [edit]

The development of a potentially life-threatening serotonin syndrome (also more recently classified as
"serotonin toxicity")[35] may occur with venlafaxine treatment, particularly with concomitant use of
serotonergic drugs (including but not limited to SSRI and SNRI)s, many hallucinogens such as
tryptamines and phenethylamines (LSD/LSA, DMT, MDMA, MDPV, mescaline for example),
dextromethorphan (DXM)/dextrorphan (DXO), tramadol, tapentadol, meperidine/pethidine and
triptans) and with drugs that impair metabolism of serotonin (including MAOIs). Serotonin syndrome
symptoms may include mental status changes (e.g., agitation, hallucinations, coma), autonomic
instability (e.g., tachycardia, labile blood pressure, hyperthermia), neuromuscular aberrations (e.g.,
hyperreflexia, incoordination) and/or gastrointestinal symptoms (e.g., nausea, vomiting, diarrhea).
Venlafaxine-induced serotonin syndrome has also been reported when venlafaxine has been taken in
isolation in overdose. [36] An abortive serotonin syndrome state, in which some but not all of the
symptoms of the full serotonin syndrome are present, has been reported with venlafaxine at mid-
range dosages (150 mg per day) [37] A case of a patient with serotonin syndrome induced by low-
dose venlafaxine (37.5 mg per day) has also been reported. [38]

Combined serotonin toxicity and SSRI discontinuation syndrome [edit]

(SSRI withdrawal)
Venlafaxine may be particularly hazardous to those individuals who are susceptible to both
venlafaxine-induced serotonin toxicity (also known as serotonin syndrome) and SSRI discontinuation

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syndrome. In such cases, individuals who have developed the potentially fatal serotonin toxicity
and/or may be at risk of doing so, may find cessation or dose reduction unachievable, placing them at
continuing risk. As it is not possible to determine which patients are likely to develop the most severe
symptoms of the discontinuation syndrome before cessation or dose reduction is attempted, this dual
risk requires that all patients are closely monitored during any increase in dosage (when the patient
is most at risk of developing serotonin toxicity) [39] and that such increases are carried out in the
smallest incremental steps possible. Additionally, patients who recommence venlafaxine or revert to a
higher dosage following a failed attempt to discontinue the drug or reduce dosage are another group
with an increased risk of developing serotonin toxicity. [34]

Available forms [edit]

Effexor is distributed in pentagon-shaped, peach-colored tablets of

25 mg, 37.5 mg, 50 mg, 75 mg, and 100 mg. There is also an
extended-release version distributed in capsules of 37.5 mg
(gray/peach), 75 mg (peach), and 150 mg (brownish red).

Venlafaxine extended release (XR) [edit]

Venlafaxine extended release is chemically the same as normal

venlafaxine. The extended release version (sometimes referred to as
controlled release and made on spheronization equipment from Caleva
Process Solutions) controls the release of the drug into the
Effexor XR 75 mg and
gastrointestinal tract over a longer period than normal venlafaxine. This 150 mg capsules
results in a lower peak plasma concentration. Studies have shown that
the extended release formula has a lower incidence of patients
suffering from nausea as a side effect, resulting in a lower number of
patients stopping their treatment due to nausea.[40] In Australia, New
Zealand and Switzerland, Wyeth sells their venlafaxine XR tablets
under the name "Efexor-XR" (note the spelling with one 'f', rather than
"Effexor-XR"). In Brazil, Medley sells a venlafaxine XR capsule under
the brand name Alenthus XR. In September 2008, Osmotica
Pharmaceuticals began marketing venlafaxine extended release tablets
in the United States to compete with Wyeth's capsule-form, Effexor- Generic 75mg (top) and
150mg (bottom) venlafaxine
XR. Sales of branded Efexor XR have remained strong, at
capsules by Krka
US$2.7bn. [41] Teva may begin to offer generic Effexor XR in the US
on July 1, 2010, per a settlement agreement with Wyeth, but will have
to pay Wyeth a portion of the sale price, driving up the cost. [42] Impax may begin to offer generic
Effexor XR in the US on July 1, 2011, per a settlement agreement with Wyeth, but, like Teva, will
have to pay Wyeth a portion of the sale price.[43]

Generic [edit]

Generic venlafaxine is available in the United States as of August 2006 and in Canada as of
December 2006 due to patent expiry. Generic forms of the extended-release version have been
available in Canada as of January 2007 and currently include Co Venlafaxine XR (Cobalt
Pharmaceuticals Inc.), Gen-Venlafaxine XR (Genpharm), Riva-Venlafaxine XR (Laboratoire Riva
Inc.), Novo Venlafaxine XR (Novopharm Limited), PMS-Venlafaxine XR (Pharmascience Inc.), Ratio-
Venlafaxine XR (ratiopharm), Viepax (in Israel) and Sandoz Venlafaxine XR (Sandoz Canada Inc.).
Generic versions of both drug forms are available now in India. Generic versions are also available in
the UK such as Vaxalin manufactured by RatioPharm GmbH. [44] On May 7, 2010 the Canadian
pharmaceutical company IntelliPharmaCeutics Inc. announced that the FDA had accepted its filing for
a generic version of Venlafaxine XR utilizing its own proprietary technologies.[45]

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Overdose [edit]

Most patients overdosing with venlafaxine develop only mild symptoms. However, severe toxicity is
reported, with the most common symptoms being CNS depression, serotonin toxicity, seizure, or
cardiac conduction abnormalities.[46] Venlafaxine's toxicity appears to be higher than other SSRIs,
with a fatal toxic dose closer to that of the tricyclic antidepressants than the SSRIs. Doses of 900 mg
or more are likely to cause moderate toxicity. [47] Deaths have been reported following very large
doses. [48][49] Plasma venlafaxine concentrations in overdose survivors have ranged from 6–24 mg/l,
while postmortem blood levels in fatalities are often in the 10–90 mg/l range.[50]
On May 31, 2006, The Medicines and Healthcare Products Regulatory Agency (MHRA) UK has
concluded its review into all the latest safety evidence relating to venlafaxine, and particularly looked
at the risks associated with overdose. The advice is: the need for specialist supervision in those
severely depressed or hospitalized patients who need doses 300 mg or more; cardiac
contraindications are more targeted towards high risk groups; patients with uncontrolled hypertension
should not take venlafaxine, and blood pressure monitoring is recommended for all patients; and
updated advice on possible drug interactions. [51]
On 17 October 2006, Wyeth and the FDA notified healthcare professionals of revisions to the
Overdosage/Human Experience section of the prescribing information for Effexor (venlafaxine),
indicated for treatment of major depressive disorder. In postmarketing experience, there have been
reports of overdose with venlafaxine, occurring predominantly in combination with alcohol and/or
other drugs. Published retrospective studies report that venlafaxine overdosage may be associated
with an increased risk of fatal outcome compared to that observed with SSRI antidepressant
products, but lower than that for tricyclic antidepressants. Healthcare professionals are advised to
prescribe Effexor and Effexor XR in the smallest quantity of capsules consistent with good patient
management to reduce the risk of overdose. [52]
A report in the British Medical Journal in 2002 by Dr. Nicholas Buckley and colleagues at the
Department of Clinical Pharmacology and Toxicology, Canberra Hospital, Australia studying fatal
toxicity index (deaths per million prescriptions), found that venlafaxine's fatal toxicity is higher than
that of other serotoninergic antidepressants, but it is similar to that of some of the less toxic tricyclic
antidepressants. Overall, they found serious toxicity could occur following venlafaxine overdose with
reports of deaths, arrythmias, and seizures. They did, however, state that this type of data is open to
criticism, pointing out that mortality data may be influenced by previous literature and that "less toxic"
drugs may be preferentially prescribed to patients at higher risk of poisoning and suicide, but they are
also less likely to be listed as the sole cause of death from overdose. It also assumes that drugs are
taken in overdose with similar frequency and in similar amounts. They suggested "clinicians need to
consider whether factors in their patients reduce or compensate for this risk before prescribing
venlafaxine."[53]
The 27 February 2007 Vancouver Sun reported the BC Drug and Poison Information Centre has
alerted doctors that the drug poses a significant risk of death from overdose, saying that venlafaxine
"appears more toxic than it was originally hoped". [54] A doctor from the Department of Pharmacy
Services College of Pharmacy, Medical University of South Carolina, Charleston, South Carolina,
reported on the death of a 39-year-old patient with a 30 g overdose. [48] To put this into perspective,
a patient would have to take over 66 of the infrequently prescribed 450 mg high dosage pills, or 400
of the commonly prescribed 75 mg pills.

Management of overdose [edit]

There is no specific antidote for venlafaxine, and management is generally supportive, providing
treatment for the immediate symptoms. Administration of activated charcoal can prevent absorption of
the drug. Monitoring of cardiac rhythm and vital signs is indicated. Seizures are managed with

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benzodiazepines or other anticonvulsants. Forced diuresis, hemodialysis, exchange transfusion, or

hemoperfusion are unlikely to be of benefit in hastening the removal of venlafaxine, due to the drug's
high volume of distribution. [55]

Mechanism of action [edit]

Venlafaxine is a bicyclic antidepressant, and is usually categorized as a serotonin-norepinephrine

reuptake inhibitor (SNRI), but it has been referred to as a serotonin-norepinephrine-dopamine
reuptake inhibitor (SNDRI).[56][57] It works by blocking the transporter "reuptake" proteins for key
neurotransmitters affecting mood, thereby leaving more active neurotransmitters in the synapse. The
neurotransmitters affected are serotonin and norepinephrine. Additionally, in high doses it weakly
inhibits the reuptake of dopamine,[58] with recent evidence showing that the norepinephrine
transporter also transports some dopamine as well, implying that SNRIs may also increase dopamine
transmission. This is because SNRIs work by inhibiting reuptake, i.e. preventing the serotonin and
norepinephrine transporters from taking their respective neurotransmitters back to their storage
vesicles for later use. If the norepinephrine transporter normally recycles some dopamine too, then
SNRIs will also enhance dopaminergic transmission. However, while concurrent increase in dopamine
(particularly in the prefrontal cortex) is likely to occur, [59] the antidepressant effects of any drug are
believed to result largely from the modulation of serotonin and norepinephrine; dopamine is thought to
play a comparatively small role in depression. [60]

Pharmacokinetics [edit]

Venlafaxine is well absorbed, with at least 92% of an oral dose being absorbed into systemic
circulation. It is extensively metabolized in the liver via the CYP2D6 isoenzyme to desvenlafaxine (O-
desmethylvenlafaxine), which is just as potent a serotonin-norepinephrine reuptake inhibitor as the
parent compound, meaning that the differences in metabolism between extensive and poor
metabolizers are not clinically important in terms of efficacy. Side effects, however, are reported to be
more severe in CYP2D6 poor metabolizers. [61] Steady-state concentrations of venlafaxine and its
metabolite are attained in the blood within 3 days. Therapeutic effects are usually achieved within 3
to 4 weeks. No accumulation of venlafaxine has been observed during chronic administration in
healthy subjects. The primary route of excretion of venlafaxine and its metabolites is via the
kidneys.[6] The half-life of venlafaxine is relatively short, and, therefore, patients are directed to
adhere to a strict medication routine, avoiding missing a dose. Even a single missed dose can result
in the withdrawal symptoms.[32]

Carriers of the (T;T) allele of rs2032583 [62] SNP in the ABCB1 gene are seven times less likely to
respond to venlafaxine treatment. This genetic variant is present in about two-thirds of people of
European descent and 80% to 90% of East Asians.

Drug interactions [edit]

Venlafaxine should be taken with caution when using St John's wort.[63] Venlafaxine may lower the
seizure threshold, and coadministration with other drugs that lower the seizure threshold such as
bupropion and tramadol should be done with caution and at low doses. [64]
There have been false positive phencyclidine (PCP) results caused by venlafaxine, with certain on-
site routine urine-based drug tests. [65][66]
Although the synergistic effects may not be as bad as with other antidepressants, it is still not
recommended to take venlafaxine with alcohol.[67]

Physical/chemical properties [edit]

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The chemical structure of venlafaxine is designated (R/S)-1-[2-(dimethylamino)-1-(4
methoxyphenyl)ethyl] cyclohexanol hydrochloride or (±)-1-[a [a- (dimethylamino)methyl] p-
methoxybenzyl] cyclohexanol hydrochloride, and it has the empirical formula of C 17 H 27 NO 2 . It is a
white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the
atypical opioid analgesic tramadol, and more distantly the newly-released opioid tapentadol, but not
to any of the conventional antidepressant drugs, including tricyclic antidepressants, SSRIs, MAOIs, or
RIMAs. [47]
See also
Desvenlafaxine
Tramadol
References
Notes
1. ^ a b c Laurence L Brunton, ed (2006).
Goodman & Gilman's The Pharmacological
Basis of Therapeutics (11th ed.). New York:
McGraw-Hill Medical Publishing Division.
ISBN 0-07-142280-3.
2. ^ Muth EA, Haskins JT, Moyer JA, Husbands
GE, Nielsen ST, Sigg EB (December 1986).
"Antidepressant biochemical profile of the novel
bicyclic compound Wy-45,030, an ethyl
cyclohexanol derivative" . Biochemical
Pharmacology 35 (24): 4493–7.
doi:10.1016/0006-2952(86)90769-0 .
PMID 3790168 .
3. ^ Yardley JP, Husbands GE, Stack G, et al.
(October 1990). "2-Phenyl-2-(1-
hydroxycycloalkyl)ethylamine derivatives:
synthesis and antidepressant activity". Journal
of Medicinal Chemistry 33 (10): 2899–905.
doi:10.1021/jm00172a035 .
PMID 1976813 .
4. ^ Bymaster FP, Dreshfield-Ahmad LJ,
Threlkeld PG, et al. (December 2001).
"Comparative affinity of duloxetine and
venlafaxine for serotonin and norepinephrine
transporters in vitro and in vivo, human
serotonin receptor subtypes, and other
neuronal receptors".
Neuropsychopharmacology : Official Publication
of the American College of
Neuropsychopharmacology 25 (6): 871–80.
doi:10.1016/S0893-133X(01)00298-6 .
PMID 11750180 .
5. ^ The number of prescriptions was calculated
as the total of prescriptions for the
corresponding generic and brand-name drugs
using data from the charts for generic and
brand-name drugs. "Top 200 generic drugs by
units in 2007." . Drug Topics, Feb 18, 2008.
Retrieved 2008-10-23. "Top 200 brand drugs
http://en.wikipedia.org/wiki/Venlafaxine[1/12/2011 3:46:52 PM]
[edit]
[edit]
PMID 17420682 .
29. ^ Brent DA, Emslie GJ, Clarke GN, et al. (April
2009). "Predictors of spontaneous and
systematically assessed suicidal adverse
events in the treatment of SSRI-resistant
depression in adolescents (TORDIA) study".
Am J Psychiatry 166 (4): 418–26.
doi:10.1176/appi.ajp.2008.08070976 .
PMID 19223438 .
30. ^ Harrison CL, Ferrier N, Young AH (June
2004). "Tolerability of high-dose venlafaxine in
depressed patients". J. Psychopharmacol.
(Oxford) 18 (2): 200–4.
doi:10.1177/0269881104042621 .
PMID 15260908 .
31. ^ a b c Haddad PM (2001). "Antidepressant
discontinuation syndromes". Drug Saf 24 (3):
183–97. doi:10.2165/00002018-200124030-
00003 . PMID 11347722 .
32. ^ a b Parker G, Blennerhassett J (1998).
"Withdrawal reactions associated with
venlafaxine". Aust N Z J Psychiatry 32 (2): 291–
4. doi:10.3109/00048679809062742 .
PMID 9588310 .
33. ^ Fava M, Mulroy R, Alpert J, Nierenberg A,
Rosenbaum J (1997). "Emergence of adverse
events following discontinuation of treatment
with extended-release venlafaxine". Am J
Psychiatry 154 (12): 1760–2. PMID 9396960 .
34. ^ a b Double D (1997). "Prescribing
antidepressants in general practice. People
may become psychologically dependent on
antidepressants" . BMJ 314 (7083): 829.
PMID 9081020 .
35. ^ Dunkley EJ, Isbister GK, Sibbritt D, Dawson
AH, Whyte IM (September 2003). "The Hunter
Serotonin Toxicity Criteria: simple and accurate
diagnostic decision rules for serotonin
Venlafaxine - Wikipedia, the free encyclopedia

toxicity" . QJM 96 (9): 635–42.

by units in 2007." . Drug Topics, Feb 18,
doi:10.1093/qjmed/hcg109 .
2008. Retrieved 2008-10-23.
PMID 12925718 .
6. ^ a b c d e f g h i "Effexor Medicines Data 36. ^ Kolecki P (1997). "Isolated venlafaxine-
Sheet" . Wyeth Pharmaceuticals Inc. 2006. induced serotonin syndrome". J Emerg Med 15
Retrieved 17 September 2006. (4): 491–3. doi:10.1016/S0736-4679(97)00078-
7. ^ Golden RN, Nicholas L (2000). 4 . PMID 9279702 .
"Antidepressant efficacy of venlafaxine". 37. ^ Ebert D. et al.. "Hallucinations as a side effect
Depression and anxiety 12 Suppl 1: 45–9. of venlafaxine treatment" . Psychiatry On-line.
doi:10.1002/1520-6394(2000)12:1 (inactive Retrieved 2008-06-17.
2010-07-26). PMID 11098413 . 38. ^ Pan JJ, Shen WW (February 2003).
8. ^ Thase ME, Clayton AH, Haight BR, "Serotonin syndrome induced by low-dose
Thompson AH, Modell JG, Johnston JA (2006).
venlafaxine". Ann Pharmacother 37 (2): 209–
"A double-blind comparison between bupropion
11. doi:10.1345/aph.1C021 .
XL and venlafaxine XR: sexual functioning, PMID 12549949 .
antidepressant efficacy, and tolerability".
39. ^ Venlafaxine (marketed as Effexor) FDA Alert:
Journal of clinical psychopharmacology 26 (5): SSRIs/SNRI/Triptan and Serotonin Syndrome
482–8. [issued 7/2006]
doi:10.1097/01.jcp.0000239790.83707.ab .
40. ^ DeVane CL. (2003). "Immediate-release
PMID 16974189 .
versus controlled-release formulations:
9. ^ Lenox-Smith AJ, Jiang Q (2008).
pharmacokinetics of newer antidepressants in
"Venlafaxine extended release versus
relation to nausea". J Clin Psychiatry 64 (Suppl
citalopram in patients with depression
18): 14–9. PMID 14700450 .
unresponsive to a selective serotonin reuptake
41. ^ Details for Effexor XR
inhibitor". Int Clin Psychopharmacol 23 (3):
42. ^
113–9. doi:10.1097/YIC.0b013e3282f424c2 .
http://www.wyeth.com/irj/servlet/prt/portal/prtroot/
PMID 18408525 .
(Archived by WebCite® at
10. ^ Rowbotham M, Goli V, Kunz N, Lei D (2004).
http://www.webcitation.org/5pXQuFykU ) p. 3,
"Venlafaxine extended release in the treatment
4
of painful diabetic neuropathy: a double-blind,
43. ^ http://www.wyeth.com/irj/portal/news/archive?
placebo-controlled study". Pain 110 (3): 697–
nav=display&navTo=/wyeth_html/home/news/pre
706. doi:10.1016/j.pain.2004.05.010 .
44. ^ [1]
PMID 15288411 .
45. ^ [2]
11. ^ Ozyalcin S, Talu G, Kiziltan E, Yucel B, Ertas
46. ^ Blythe D, Hackett L (1999). "Cardiovascular
M, Disci R (2005). "The efficacy and safety of
and neurological toxicity of venlafaxine". Hum
venlafaxine in the prophylaxis of migraine".
Exp Toxicol 18 (5): 309–13.
Headache 45 (2): 144–52. doi:10.1111/j.1526-
doi:10.1191/096032799678840165 .
4610.2005.05029.x . PMID 15705120 .
PMID 10372752 .
12. ^ Mayo Clinic staff (2005). "Beyond hormone
47. ^ a b Whyte I, Dawson A, Buckley N (2003).
therapy: Other medicines may help" . Hot
"Relative toxicity of venlafaxine and selective
flashes: Ease the discomfort of menopause.
serotonin reuptake inhibitors in overdose
Mayo Clinic. Retrieved 19 August 2005.
compared to tricyclic antidepressants". QJM 96
13. ^ Schober C, Ansani N (2003). "Venlafaxine
(5): 369–74. doi:10.1093/qjmed/hcg062 .
hydrochloride for the treatment of hot flashes".
PMID 12702786 .
Ann Pharmacother 37 (11): 1703–7.
48. ^ a b Mazur J, Doty J, Krygiel A (2003). "Fatality
doi:10.1345/aph.1C483 . PMID 14565812 .
related to a 30-g venlafaxine overdose".
14. ^ "Medications" . Stanford University School
Pharmacotherapy 23 (12): 1668–72.
of Medicine, Center for Narcolepsy. Revised
doi:10.1592/phco.23.15.1668.31951 .
02/07/2003. Retrieved 2007-09-03.
PMID 14695048 .
15. ^ Albert U, Aguglia E, Maina G, Bogetto F
49. ^ Banham N (1998). "Fatal venlafaxine
(November 2002). "Venlafaxine versus
overdose". Med J Aust 169 (8): 445, 448.
clomipramine in the treatment of obsessive-
PMID 9830400 .
compulsive disorder: a preliminary single-blind,
12-week, controlled study" (PDF). J Clin 50. ^ R. Baselt, Disposition of Toxic Drugs and
Psychiatry 63 (11): 1004–9. PMID 12444814 . Chemicals in Man, 8th edition, Biomedical
Publications, Foster City, CA, 2008, pp. 1634-
16. ^ Hain T (Revised 12/30/2007). "Orthostatic

http://en.wikipedia.org/wiki/Venlafaxine[1/12/2011 3:46:52 PM]

Venlafaxine - Wikipedia, the free encyclopedia
Hypotension" . www.dizziness-and-
balance.com. Retrieved 2008-03-29.
17. ^ Courtney D (2004). "Selective serotonin
reuptake inhibitor and venlafaxine use in
children and adolescents with major depressive
disorder: a systematic review of published
randomized controlled trials". Can J Psychiatry
49 (8): 557–63. PMID 15453105 .
18. ^ "Use of antidepressants during pregnancy
and the risk of spontaneous abortion" ,
Canadian Medical Association Journal
19. ^ Gentile S (2005). "The safety of newer
antidepressants in pregnancy and
breastfeeding". Drug Saf 28 (2): 137–52.
doi:10.2165/00002018-200528020-00005 .
PMID 15691224 .
20. ^ de Moor R, Mourad L, ter Haar J, Egberts A
(2003). "[Withdrawal symptoms in a neonate
following exposure to venlafaxine during
pregnancy]". Ned Tijdschr Geneeskd 147 (28):
1370–2. PMID 12892015 .
21. ^ Ferreira E, Carceller AM, Agogué C, Martin
BZ, St-André M, Francoeur D, Bérard A (2007).
"[Effects of selective serotonin reuptake
inhibitors and venlafaxine during pregnancy in
term and preterm neonates]". Pediatrics 119
(1): 52–9. doi:10.1542/peds.2006-2133 .
PMID 17200271 .
22. ^ Moses-Kolko EL, Bogen D, Perel J, Bregar
A, Uhl K, Levin B, Wisner KL (2005). "[Neonatal
signs after late in utero exposure to serotonin
reuptake inhibitors: Literature review and
implications for clinical applications]". JAMA
293 (19): 2372–83.
doi:10.1001/jama.293.19.2372 .
PMID 15900008 .
23. ^ Broy, P; Bérard, A (2010). "Gestational
exposure to antidepressants and the risk of
spontaneous abortion: a review". Current drug
delivery 7 (1): 76–92.
doi:10.2174/156720110790396508 .
PMID 19863482 .  edit
24. ^ Nakhai-Pour, H. R.; Broy, P.; Berard, A.
(2010). "Use of antidepressants during
pregnancy and the risk of spontaneous
abortion" . Canadian Medical Association
Journal 182 (10): 1031.
doi:10.1503/cmaj.091208 .
PMID 20513781 . Lay summary .  edit
25. ^ Tiihonen J, Lönnqvist J, Wahlbeck K, Klaukka
T, Tanskanen A, Haukka J (2006).
"Antidepressants and the risk of suicide,
attempted suicide, and overall mortality in a
nationwide cohort". Arch. Gen. Psychiatry 63
(12): 1358–67.
http://en.wikipedia.org/wiki/Venlafaxine[1/12/2011 3:46:52 PM]
1637.
51. ^ MHRA UK (31 May 2006). "Updated product
information for venlafaxine". Safeguarding
public health 120: 778.
doi:10.1016/j.puhe.2006.03.006 .
52. ^ "Wyeth Letter to Health Care Providers" .
Wyeth Pharmaceuticals Inc. 2006. Retrieved
2009-08-06.
53. ^ Buckley N, McManus P (2002). "Fatal toxicity
of serotoninergic and other antidepressant
drugs: analysis of United Kingdom mortality
data" . BMJ 325 (7376): 1332–3.
doi:10.1136/bmj.325.7376.1332 .
PMID 12468481 .
54. ^ Fayerman, Pamela (February 27, 2007).
"Warning issued over drug" . Vancouver Sun.
Retrieved 2007-06-02.
55. ^ Hanekamp B, Zijlstra J, Tulleken J,
Ligtenberg J, van der Werf T, Hofstra L (2005).
"Serotonin syndrome and rhabdomyolysis in
venlafaxine poisoning: a case report". Neth J
Med 63 (8): 316–8. PMID 16186642 .
56. ^ [No Authors listed]. "Acute Effectiveness of
Additional Drugs to the Standard Treatment of
Depression" . ClinicalTrials.gov. Retrieved 23
June 2005.
57. ^ Goeringer K, McIntyre I, Drummer O (2001).
"Postmortem tissue concentrations of
venlafaxine". Forensic Sci Int 121 (1-2): 70–5.
doi:10.1016/S0379-0738(01)00455-8 .
PMID 11516890 .
58. ^ Wellington K, Perry C (2001). "Venlafaxine
extended-release: a review of its use in the
management of major depression". CNS Drugs
15 (8): 643–69. doi:10.2165/00023210-
200115080-00007 . PMID 11524036 .
59. ^
http://stahlonline.cambridge.org/prescribers_drug
page=0521683505c95_p539-
544.html.therapeutics&name=Venlafaxine&title=T
60. ^ Delgado, P.L.; Moreno, F.A. (2000). "Role of
norepinephrine in depression". Journal of
Clinical Psychiatry 61: 5–12.
PMID 10703757 .
61. ^ Shams ME et al. (2006). "CYP2D6
polymorphism and clinical effect of the
antidepressant venlafaxine". J Clin Pharm Ther
31 (5): 493–502. doi:10.1111/j.1365-
2710.2006.00763.x . PMID 16958828 .
62. ^ SNPedia
63. ^ Karch, Amy (2006). 2006 Lippincott's Nursing
Drug Guide. Philadephia, Baltimore, New York,
London, Buenos Aires, Hong Kong, Sydney,
Tokyo: Lippincott Williams & Wilkins. ISBN 1-
58255-436-6.
Venlafaxine - Wikipedia, the free encyclopedia

doi:10.1001/archpsyc.63.12.1358 . 64. ^ Thundiyil JG, Kearney TE, Olson KR (March

PMID 17146010 .
26. ^ Rubino A, Roskell N, Tennis P, Mines D,
Weich S, Andrews E (2007). "Risk of suicide
during treatment with venlafaxine, citalopram,
fluoxetine, and dothiepin: retrospective cohort
study" . BMJ 334 (7587): 242.
doi:10.1136/bmj.39041.445104.BE .
PMID 17164297 .
27. ^ a b "Overview for December 13 Meeting of
Psychopharmacologic Drugs Advisory
Committee" (PDF). November 16, 2006.
Retrieved 2007-06-20.
28. ^ Emslie GJ, Findling RL, Yeung PP, Kunz NR,
Li Y (2007). "Venlafaxine ER for the treatment
of pediatric subjects with depression: results of
two placebo-controlled trials". Journal of the
American Academy of Child and Adolescent
Psychiatry 46 (4): 479–88.
doi:10.1097/chi.0b013e31802f5f03 .
2007). "Evolving epidemiology of drug-induced
seizures reported to a Poison Control Center
System". J Med Toxicol 3 (1): 15–9.
doi:10.1007/BF03161033 .
PMID 18072153 .
65. ^ Santos PM, López-García P, Navarro JS,
Fernández AS, Sádaba B, Vidal JP (February
2007). "False positive phencyclidine results
caused by venlafaxine" . Am J Psychiatry 164
(2): 349. doi:10.1176/appi.ajp.164.2.349 .
PMID 17267806 .
66. ^ Sena SF, Kazimi S, Wu AH (2002). "False-
positive phencyclidine immunoassay results
caused by venlafaxine and O-
desmethylvenlafaxine" . Clin. Chem. 48 (4):
676–7. PMID 11901076 .
67. ^ http://www.nhs.uk/chq/Pages/863.aspx?
CategoryID=73&SubCategoryID=103

External links [edit]

Drug information
U.S. Food and Drug Administration information on Effexor
Efexor patient information leaflet Efexor patient information leaflet
Effexor XR prescribing information for healthcare professionals (pdf) (USA only)
Detailed Patient/Parent Information on Effexor
List of international brand names for Venlafaxine
U.S. National Library of Medicine: Drug Information Portal - Venlafaxine
Diagnostic tools
The Hunter Serotonin Toxicity Criteria: simple and accurate diagnostic decision rules for serotonin
toxicity

Patient experiences [edit]

Stutz, Bruce "Self-Nonmedication" New York Times Magazine May 6, 2007

  Articles and topics related to Venlafaxine

v·d·e Antidepressants (N06A)

  Specific reuptake inhibitors (RIs), enhancers (REs), and releasing agents (RAs)

Alaproclate • Citalopram • Escitalopram • Femoxetine •

Selective serotonin reuptake inhibitors (SSRIs)
Serotonin-norepinephrine reuptake inhibitors (SNRIs)
Fluoxetine • Fluvoxamine • Indalpine • Ifoxetine •
Litoxetine • Lubazodone • Panuramine • Paroxetine •
Pirandamine • Seproxetine • Sertraline • Vilazodone •
Zimelidine
Bicifadine • Clovoxamine • Desvenlafaxine •
Duloxetine • Levomilnacipran • Eclanamine •
Milnacipran • Sibutramine • Venlafaxine
Brasofensine • BTS-74,398 • Cocaine • Diclofensine •
DOV-21,947 • DOV-102,677 • DOV-216,303 •

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Venlafaxine - Wikipedia, the free encyclopedia

Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs) EXP-561 • Fezolamine • JNJ-7,925,476 • NS-2359 •

Norepinephrine reuptake inhibitors (NRIs)
Dopamine reuptake inhibitors (DRIs)
PRC200-SS • Pridefrine • SEP-225,289 •
SEP-227,162 • Tesofensine
Amedalin • Atomoxetine/Tomoxetine • Binedaline •
Ciclazindol • Daledalin • Esreboxetine • Lortalamine •
Mazindol • Nisoxetine • Reboxetine • Talopram •
Talsupram • Tandamine • Viloxazine
Medifoxamine • Vanoxerine

Amineptine • Bupropion/Amfebutamone • Cilobamine •

Norepinephrine-dopamine reuptake inhibitors (NDRIs)
Norepinephrine-dopamine releasing agents (NDRAs)
Serotonin-norepinephrine-dopamine releasing agents (SNDRAs)
Manifaxine • Methylphenidate • Nomifensine •
Radafaxine • Tametraline
Amphetamine • Befuraline • Lisdexamfetamine •
Methamphetamine • Phenethylamine • Piberaline •
Tranylcypromine
4-Methyl-αMT • αET/Etryptamine • αMT/Metryptamine

Selective serotonin reuptake enhancers (SSREs) Tianeptine

Others Indeloxazine • Tramadol • Viqualine

  Receptor antagonists and/or reuptake inhibitors

Serotonin antagonists and reuptake inhibitors (SARIs) Etoperidone • Nefazodone • Trazodone

Aptazapine • Esmirtazapine • Mianserin •

Noradrenergic and specific serotonergic antidepressants (NaSSAs)
Mirtazapine • Setiptiline/Teciptiline
Norepinephrine-dopamine disinhibitors (NDDIs) Agomelatine

Serotonin modulators and stimulators (SMSs) Lu AA21004

  Tricyclic and tetracyclic antidepressants (TCAs/TeCAs)

Tricyclics: Amezepine • Amineptine • Amitriptyline • Amitriptylinoxide • Azepindole • Butriptyline • Cianopramine •

Clomipramine • Cotriptyline • Cyanodothiepin • Demexiptiline • Depramine/Balipramine • Desipramine • Dibenzepine •
Dimetacrine • Dosulepin/Dothiepin • Doxepin • Enprazepine • Fluotracen • Hepzidine • Homopipramol • Imipramine •
Imipraminoxide • Intriptyline • Iprindole • Ketipramine • Litracen • Lofepramine • Losindole • Mariptiline • Melitracen •
Metapramine • Mezepine • Naranol • Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Pipofezine •
Propizepine • Protriptyline • Quinupramine • Tampramine • Tianeptine • Tienopramine • Trimipramine; Tetracyclics:
7-OH-Amoxapine • Amoxapine • Aptazapine • Azipramine • Ciclazindol • Ciclopramine • Esmirtazapine • Loxapine •
Maprotiline • Mazindol • Mianserin • Mirtazapine • Oxaprotiline • Setiptiline/Teciptiline

  Monoamine oxidase inhibitors (MAOIs)

Nonselective: Irreversible: Benmoxin • Echinopsidine • Iproclozide • Iproniazid • Isocarboxazid • Mebanazine •

Metfendrazine • Nialamide • Octamoxin • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine •
Safrazine • Tranylcypromine; Reversible: Caroxazone • Paraxazone; MAO A -Selective: Irreversible: Clorgyline;
Reversible: Amiflamine • Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Esuperone •
Harmala Alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene Blue •
Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone • Tyrima; MAOB -
Selective: Irreversible: Ladostigil • Mofegiline • Pargyline • Rasagiline • Selegiline; Reversible: Lazabemide •
Milacemide

  Azapirones and other 5-HT1A receptor agonists

Alnespirone • Aripiprazole • Befiradol • Buspirone • Eptapirone • Flesinoxan • Flibanserin • Gepirone • Ipsapirone •

Oxaflozane • Tandospirone • Vilazodone • Zalospirone

  Dietary supplements (vitamins, minerals, amino acids, etc)

Ascorbic acid (Vitamin C) • Fish oil • Folic acid (Vitamin B 9 ) • L-5-HTP (Oxitriptan) • L-DOPA (Levodopa) •
L-Methionine • L-Phenylalanine • L-Tryptophan • L-Tyrosine • Lithium • Magnesium • Melatonin • Niacin/Niacinamide
(Vitamin B 3 ) • Omega-3 fatty acids • Pyridoxine (Vitamin B 6 ) • Rubidium • SAMe • Zinc

http://en.wikipedia.org/wiki/Venlafaxine[1/12/2011 3:46:52 PM]

Venlafaxine - Wikipedia, the free encyclopedia

  Research compounds and miscellaneous agents

5 -HT4 R agonists RS-67,333 • SL65.0155

5 -HT7 R antagonists Amisulpride

α2δ-VDCC blockers Gabapentin • Pregabalin

β 3 -Adrenoceptor agonists Amibegron • Solabegron

σ 1 R agonists Afobazole • Dextromethorphan • Fluvoxamine • Igmesine • Opipramol • PRE-084

CB1 R agonists Nabilone • Tetrahydrocannabinol/Dronabinol

COMT inhibitors Entacapone • Tolcapone

CRF 1 R antagonists Antalarmin • CP-154,526 • Pexacerfont • Pivagabine

D 2 /D 3 AR antagonists Amisulpride • Sulpiride

D 2 /D 3 /D 4 R agonists Piribedil • Pramipexole • Ropinirole • Rotigotine • Roxindole

DOR agonists BU-48 • Buprenorphine • BW373U86 • DPI-287 • Heroin • Kratom • SNC-80

Enkephalinase inhibitors D-Phenylalanine • RB-101

FAAH inhibitors Acetaminophen/Paracetamol • AM-404 • URB-597

KOR antagonists 5-GNTI • Buprenorphine • JDTic • Norbinaltorphimine

Buprenorphine • Codeine • Dextropropoxyphene • Dihydrocodeine • Fentanyl • Heroin •

MOR agonists Hydrocodone • Hydromorphone • Kratom • Methadone • Morphine • Opium • Oxycodone •
Oxymorphone • Pethidine/Meperidine • Tapentadol • Tramadol
MT1 /MT2 R agonists Agomelatine • Melatonin • Ramelteon • Tasimelteon

NK1 R antagonists Aprepitant • Casopitant • Fosaprepitant • L-733,060 • Maropitant • Vestipitant

NMDAR antagonists Dextromethorphan • Ketamine • Magnesium • Memantine • Zinc

PDE4 inhibitors Mesembrine (Kanna) • Rolipram

TRPC6 activators Adhyperforin (St. John's Wort) • Hyperforin (St. John's Wort)

M: PSO/PSI mepr dsrd (o, p, m, p, a, d, s), proc, drug(N5A/5B/5C/6A/6B/6D)

sysi/epon, spvo

v·d·e Anxiolytics (N05B)

Adinazolam • Alprazolam • Bretazenil • Bromazepam • Camazepam •
Chlordiazepoxide • Clobazam • Clonazepam • Clorazepate • Clotiazepam •
Benzodiazepine Cloxazolam • Diazepam • Ethyl Loflazepate • Etizolam • Fludiazepam •
Halazepam • Imidazenil • Ketazolam • Lorazepam • Medazepam •
Nordazepam • Oxazepam • Pinazepam • Prazepam

Emylcamate • Mebutamate • Meprobamate (Carisoprodol, Tybamate) •

Carbamates
Phenprobamate • Procymate

GABA A PAMs Abecarnil • Adipiplon • Alpidem • CGS-9896 • CGS-20625 • Divaplon •

ELB-139 • Fasiplon • GBLD-345 • Gedocarnil • L-838,417 • NS-2664 •
Nonbenzodiazepines NS-2710 • Ocinaplon • Pagoclone • Panadiplon • Pipequaline • RWJ-51204
• SB-205,384 • SL-651,498 • Taniplon • TP-003 • TP-13 • TPA-023 •
Y-23684 • ZK-93423

Pyrazolopyridines Cartazolate • Etazolate • ICI-190,622 • Tracazolate

Chlormezanone • Ethanol (Alcohol) • Etifoxine • Kavalactones (Kava Kava)

Others
• Skullcap • Valerenic Acid (Valerian)

α 2 δ VDCC Blockers Gabapentin • Pregabalin

5-HT 1A Agonists Azapirones: Buspirone • Gepirone • Tandospirone; Others: Flesinoxan • Oxaflozane

Diphenylmethanes: Captodiame • Hydroxyzine; Others: Brompheniramine • Chlorpheniramine •

H 1 Antagonists
Pheniramine

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CRH 1 Antagonists Antalarmin • CP-154,526 • Pexacerfont • Pivagabine

NK 2 Antagonists GR-159,897 • Saredutant

MCH1 antagonists ATC-0175 • SNAP-94847

mGluR2 /3 Agonists Eglumegad

mGluR5 NAMs Fenobam

TSPO agonists DAA-1097 • DAA-1106 • Emapunil • FGIN-127 • FGIN-143

σ1 agonists Afobazole • Opipramol

Benzoctamine • Carbetocin • Demoxytocin • Mephenoxalone • Mepiprazole • Oxanamide • Oxytocin •

Others
Promoxolane • Tofisopam • Trimetozine • WAY-267,464
# WHO-EM. ‡ Withdrawn from market. Clinical trials: † Phase III. § Never to phase III

M: PSO/PSI mepr dsrd (o, p, m, p, a, d, s), proc, drug(N5A/5B/5C/6A/6B/6D)

sysi/epon, spvo

v·d·e Adrenergics

  Receptor ligands

Agonists: 5-FNE • 6-FNE • Amidephrine • Anisodamine • Anisodine • Cirazoline • Dipivefrine • Dopamine • Ephedrine •
Epinephrine (Adrenaline) • Etilefrine • Ethylnorepinephrine • Indanidine • Levonordefrin • Metaraminol • Methoxamine •
Methyldopa • Midodrine • Naphazoline • Norepinephrine (Noradrenaline) • Octopamine • Oxymetazoline • Phenylephrine •
Phenylpropanolamine • Pseudoephedrine • Synephrine • Tetrahydrozoline
Antagonists: Abanoquil • Adimolol • Ajmalicine • Alfuzosin • Amosulalol • Arotinolol • Atiprosin • Benoxathian •
Buflomedil • Bunazosin • Carvedilol • CI-926 • Corynanthine • Dapiprazole • DL-017 • Domesticine • Doxazosin •
Eugenodilol • Fenspiride • GYKI-12,743 • GYKI-16,084 • Indoramin • Ketanserin • L-765,314 • Labetalol •
α1
Mephendioxan • Metazosin • Monatepil • Moxisylyte (Thymoxamine) • Naftopidil • Nantenine • Neldazosin • Nicergoline •
Niguldipine • Pelanserin • Phendioxan • Phenoxybenzamine • Phentolamine • Piperoxan • Prazosin • Quinazosin •
Ritanserin • RS-97,078 • SGB-1,534 • Silodosin • SL-89.0591 • Spiperone • Talipexole • Tamsulosin • Terazosin •
Tibalosin • Tiodazosin • Tipentosin • Tolazoline • Trimazosin • Upidosin • Urapidil • Zolertine
* Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone, trazodone , nefazodone ,

etoperidone, and mepiprazole all antagonize α 1 -adrenergic receptors as well, which contributes to their side effects such as

orthostatic hypotension.

Agonists: (R)-3-Nitrobiphenyline • 4-NEMD • 6-FNE • Amitraz • Apraclonidine • Brimonidine • Clonidine • Detomidine •

Dexmedetomidine • Dihydroergotamine • Dipivefrine • Dopamine • Ephedrine • Ergotamine • Epinephrine (Adrenaline) •
Esproquin • Etilefrine • Ethylnorepinephrine • Guanabenz • Guanfacine • Guanoxabenz • Levonordefrin • Lofexidine •
Medetomidine • Methyldopa • Mivazerol • Naphazoline • Norepinephrine (Noradrenaline) • Phenylpropanolamine •
Piperoxan • Pseudoephedrine • Rilmenidine • Romifidine • Talipexole • Tetrahydrozoline • Tizanidine • Tolonidine •
Urapidil • Xylazine • Xylometazoline
α2
Antagonists: 1-PP • Adimolol • Aptazapine • Atipamezole • BRL-44408 • Buflomedil • Cirazoline • Efaroxan •
Esmirtazapine • Fenmetozole • Fluparoxan • GYKI-12,743 • GYKI-16,084 • Idazoxan • Mianserin • Mirtazapine •
MK-912 • NAN-190 • Olanzapine • Phentolamine • Phenoxybenzamine • Piperoxan • Piribedil • Rauwolscine •
Rotigotine • SB-269,970 • Setiptiline • Spiroxatrine • Sunepitron • Tolazoline • Yohimbine
* Note that many atypical antipsychotics and azapirones like buspirone and gepirone (via metabolite 1 -PP ) antagonize α 2 -

adrenergic receptors as well.

Agonists: 2-FNE • 5-FNE • Amibegron • Arbutamine • Arformoterol • Arotinolol • BAAM • Bambuterol • Befunolol •
Bitolterol • Broxaterol • Buphenine • Carbuterol • Cimaterol • Clenbuterol • Denopamine • Deterenol • Dipivefrine •
Dobutamine • Dopamine • Dopexamine • Ephedrine • Epinephrine (Adrenaline) • Etafedrine • Etilefrine •
Ethylnorepinephrine • Fenoterol • Formoterol • Hexoprenaline • Higenamine • Indacaterol • Isoetarine • Isoprenaline
(Isoproterenol) • Isoxsuprine • Labetalol • Levonordefrin • Levosalbutamol • Mabuterol • Methoxyphenamine •
Methyldopa • N-Isopropyloctopamine • Norepinephrine (Noradrenaline) • Orciprenaline • Oxyfedrine •
Phenylpropanolamine • Pirbuterol • Prenalterol • Ractopamine • Procaterol • Pseudoephedrine • Reproterol • Rimiterol •
Ritodrine • Salbutamol (Albuterol) • Salmeterol • Solabegron • Terbutaline • Tretoquinol • Tulobuterol • Xamoterol •

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Zilpaterol • Zinterol
Antagonists: Acebutolol • Adaprolol • Adimolol • Afurolol • Alprenolol • Alprenoxime • Amosulalol • Ancarolol • Arnolol •
Arotinolol • Atenolol • Befunolol • Betaxolol • Bevantolol • Bisoprolol • Bopindolol • Bormetolol • Bornaprolol • Brefonalol •
Bucindolol • Bucumolol • Bufetolol • Buftiralol • Bufuralol • Bunitrolol • Bunolol • Bupranolol • Burocrolol • Butaxamine •
β
Butidrine • Butofilolol • Capsinolol • Carazolol • Carpindolol • Carteolol • Carvedilol • Celiprolol • Cetamolol • Cicloprolol •
Cinamolol • Cloranolol • Cyanopindolol • Dalbraminol • Dexpropranolol • Diacetolol • Dichloroisoprenaline •
Dihydroalprenolol • Dilevalol • Diprafenone • Draquinolol • Dropranolol • Ecastolol • Epanolol • Ericolol • Ersentilide •
Esatenolol • Esmolol • Esprolol • Eugenodilol • Exaprolol • Falintolol • Flestolol • Flusoxolol • Hydroxycarteolol •
Hydroxytertatolol • ICI-118,551 • Idropranolol • Indenolol • Indopanolol • Iodocyanopindolol • Iprocrolol • Isoxaprolol •
Isamoltane • Labetalol • Landiolol • Levobetaxolol • Levobunolol • Levocicloprolol • Levomoprolol • Medroxalol •
Mepindolol • Metalol • Metipranolol • Metoprolol • Moprolol • Nadolol • Nadoxolol • Nafetolol • Nebivolol • Neraminol •
Nifenalol • Nipradilol • Oberadilol • Oxprenolol • Pacrinolol • Pafenolol • Pamatolol • Pargolol • Parodilol • Penbutolol •
Penirolol • PhQA-33 • Pindolol • Pirepolol • Practolol • Primidolol • Procinolol • Pronethalol • Propafenone • Propranolol •
Ridazolol • Ronactolol • Soquinolol • Sotalol • Spirendolol • SR 59230A • Sulfinalol • TA-2005 • Talinolol • Tazolol •
Teoprolol • Tertatolol • Terthianolol • Tienoxolol • Tilisolol • Timolol • Tiprenolol • Tolamolol • Toliprolol • Tribendilol •
Trigevolol • Xibenolol • Xipranolol

  Reuptake inhibitors

Selective norepinephrine reuptake inhibitors: Amedalin • Atomoxetine (Tomoxetine) • Ciclazindol • Daledalin •

Esreboxetine • Lortalamine • Mazindol • Nisoxetine • Reboxetine • Talopram • Talsupram • Tandamine • Viloxazine;
Norepinephrine-dopamine reuptake inhibitors: Amineptine • Bupropion (Amfebutamone) • Fencamine •
Fencamfamine • Lefetamine • Levophacetoperane • LR-5182 • Manifaxine • Methylphenidate • Nomifensine •
O-2172 • Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine • Desvenlafaxine • Duloxetine •
Eclanamine • Levomilnacipran • Milnacipran • Sibutramine • Venlafaxine; Serotonin-norepinephrine-dopamine
NET
reuptake inhibitors: Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • JNJ-7925476 •
JZ-IV-10 • Methylnaphthidate • Naphyrone • NS-2359 • PRC200-SS • SEP-225,289 • SEP-227,162 • Tesofensine;
Tricyclic antidepressants: Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin •
Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic antidepressants:
Amoxapine • Maprotiline • Mianserin • Oxaprotiline • Setiptiline; Others: Cocaine • CP-39,332 • EXP-561 •
Fezolamine • Nefazodone • Nefopam • Pridefrine • Tapentadol • Tramadol • Ziprasidone

VMAT Ibogaine • Reserpine • Tetrabenazine

  Releasing agents

Morpholines: Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine; Oxazolines: 4-Methylaminorex • Aminorex •

Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also amphetamines,
cathinones, phentermines, etc): 2-OH-PEA • 4-CAB • 4-FA • 4-FMA • 4-MA • 4-MMA • Alfetamine • Amfecloral •
Amfepentorex • Amfepramone • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Me-PEA • BDB •
Benzphetamine • BOH • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • D-Deprenyl •
Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, metamfepramone) • DMA • DMMA • EBDB • Ephedrine •
Ethcathinone • Ethylamphetamine • Ethylone • Famprofazone • Fenethylline • Fenproporex • Flephedrone • Fludorex •
Furfenorex • Hordenine • IAP • IMP • L-Deprenyl (Selegiline) • Lisdexamfetamine • Lophophine • MBDB • MDA
(Tenamfetamine) • MDEA • MDMA • MDMPEA • MDOH • MDPEA • Mefenorex • Mephedrone • Mephentermine •
Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methcathinone • Methedrone • Methylone • NAP •
Ortetamine • Paredrine • pBA • pCA • Pentorex (Phenpentermine) • Phenethylamine • Pholedrine • Phenpromethamine •
Phentermine • Phenylpropanolamine • pIA • Prenylamine • Propylamphetamine • Pseudoephedrine • Tiflorex • Tyramine •
Xylopropamine • Zylofuramine; Piperazines: 2C-B-BZP • BZP • MBZP • mCPP • MDBZP • MeOPP • pFPP; Others:
2-Amino-1,2-dihydronaphthalene • 2-Aminoindane • 2-Aminotetralin • 2-Benzylpiperidine • 4-Benzylpiperidine • 5-IAI •
Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate •
Indanorex • Isometheptene • Methylhexanamine • Octodrine • Phthalimidopropiophenone • Propylhexedrine
(Levopropylhexedrine) • Tuaminoheptane

  Enzyme inhibitors

PAH 3,4-Dihydroxystyrene

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TH 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone

Anabolism AAAD Benserazide • Carbidopa • Genistein • Methyldopa

DBH Bupicomide • Disulfiram • Dopastin • Fusaric acid • Nepicastat • Phenopicolinic acid • Tropolone

PNMT CGS-19281A • SKF-64139 • SKF-7698

Nonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone • Hydralazine • Indantadol •

Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine •
Nialamide • Octamoxin • Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine •
Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A selective: Amiflamine •
Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone •
MAO Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) •
Catabolism
Methylene Blue • Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole •
Toloxatone • Tyrima; MAO-B selective: D-Deprenyl • Selegiline (L-Deprenyl) • Ladostigil •
Lazabemide • Milacemide • Mofegiline • Pargyline • Rasagiline
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown

of their precursor dopamine.

COMT Entacapone • Tolcapone

  Others

Precursors L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine • L-DOPS (Droxidopa)

Ferrous Iron (Fe2+ ) • S-Adenosyl-L-Methionine • Vitamin B 3 (Niacin, Nicotinamide → NADPH) • Vitamin B 6
Cofactors (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B 9 (Folic acid → Tetrahydrofolic acid) •
Vitamin C (Ascorbic acid) • Zinc (Zn2+ )

Activity enhancers: BPAP • PPAP; Release blockers: Bethanidine • Bretylium • Guanadrel • Guanazodine •
Others
Guanclofine • Guanethidine • Guanoxan; Toxins: Oxidopamine (6-Hydroxydopamine)

v·d·e Serotonergics

  5-HT 1 receptor ligands

Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Enilospirone • Eptapirone • Gepirone • Ipsapirone •

Perospirone • Revospirone • Tandospirone • Tiospirone • Umespirone • Zalospirone; Antidepressants: Etoperidone •
Nefazodone • Trazodone; Antipsychotics: Aripiprazole • Asenapine • Clozapine • Quetiapine • Ziprasidone;
Ergolines: Dihydroergotamine • Ergotamine • Lisuride • Methysergide • LSD; Tryptamines: 5-CT • 5-MeO-DMT •
5-MT • Bufotenin • DMT • Psilocin • Psilocybin; Others: 8-OH-DPAT • Adatanserin • Befiradol • BMY-14802 •
Cannabidiol • Dimemebfe • Ebalzotan • Eltoprazine • F-11,461 • F-12,826 • F-13,714 • F-14,679 • F-15,063 •
F-15,599 • Flesinoxan • Flibanserin • Lesopitron • Lu AA21004 • LY-293,284 • LY-301,317 • MKC-242 • NBUMP •
5-HT 1A Osemozotan • Oxaflozane • Pardoprunox • Piclozotan • Rauwolscine • Repinotan • Roxindole • RU-24,969 •
S 14,506 • S-14,671 • S-15,535 • Sarizotan • SSR-181,507 • Sunepitron • U-92016A • Urapidil • Vilazodone •
Xaliproden • Yohimbine
Antagonists: Antipsychotics: Iloperidone • Risperidone • Sertindole; Beta blockers: Alprenolol • Cyanopindolol •
Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol • Tertatolol; Others: AV965 • BMY-7378 •
CSP-2503 • Dotarizine • Flopropione • GR-46611 • Isamoltane • Lecozotan • Metitepine/Methiothepin • MPPF •
NAN-190 • PRX-00023 • Robalzotan • S-15535 • SB-649915 • SDZ 216-525 • Spiperone • Spiramide •
Spiroxatrine • UH-301 • WAY-100,135 • WAY-100,635 • Xylamidine

Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Methysergide; Piperazines: Eltoprazine • TFMPP;

Triptans: Avitriptan • Eletriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CGS-12066A •
5-HT 1B CP-93,129 • CP-94,253 • CP-135,807 • RU-24969
Antagonists: Lysergamides: Metergoline; Others: AR-A000002 • Elzasonan • GR-127,935 • Isamoltane •
Metitepine/Methiothepin • SB-216,641 • SB-224,289 • SB-236,057 • Yohimbine

Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Avitriptan • Eletriptan •

Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others:
CP-135,807 • CP-286,601 • GR-46611 • L-694,247 • L-772,405 • PNU-109,291 • PNU-142,633
5-HT 1D

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Antagonists: Lysergamides: Metergoline; Others: Alniditan • BRL-15572 • Elzasonan • GR-127,935 • Ketanserin •

LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Metitepine/Methiothepin • Ritanserin • Yohimbine •
Ziprasidone

Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-54443 • Tryptamine

5-HT 1E
Antagonists: Metitepine/Methiothepin

Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT; Others: BRL-54443 • Lasmiditan •
5-HT 1F LY-334,370
Antagonists: Metitepine/Methiothepin

  5-HT 2 receptor ligands

Agonists: Lysergamides: ALD-52 • Ergonovine • Lisuride • LA-SS-Az • LSD • LSD-Pip •

Lysergic acid 2-butyl amide • Methysergide; Phenethylamines: 25I-NBF • 25I-NBMD • 25I-NBOH • 25I-NBOMe •
2C-B • 2C-B-FLY • 2CB-Ind • 2C-C-NBOMe • 2C-E • 2C-I • 2C-TFM-NBOMe • 2C-T-2 • 2C-T-7 • 2C-T-21 •
2CBCB-NBOMe • 2CBFly-NBOMe • Bromo-DragonFLY • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline •
TCB-2 • TFMFly; Piperazines: BZP • Quipazine • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT •
5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin •
DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: AL-34662 • AL-37350A • Dimemebfe • Medifoxamine •
Oxaflozane • PNU-22394 • RH-34
5-HT 2A Antagonists: Atypical antipsychotics: Amperozide • Aripiprazole • Carpipramine • Clocapramine • Clozapine •
Gevotroline • Iloperidone • Melperone • Mosapramine • Olanzapine • Paliperidone • Pimozide • Quetiapine •
Risperidone • Sertindole • Ziprasidone • Zotepine; Typical antipsychotics: Loxapine • Pipamperone; Antidepressants:
Amitriptyline • Amoxapine • Aptazapine • Etoperidone • Mianserin • Mirtazapine • Nefazodone • Trazodone; Others:
5-I-R91150 • AC-90179 • Adatanserin • Altanserin • AMDA • APD-215 • Blonanserin • Cinanserin • CSP-2503 •
Cyproheptadine • Deramciclane • Dotarizine • Eplivanserin • Esmirtazapine • Fananserin • Flibanserin • Ketanserin •
KML-010 • Lubazodone • Mepiprazole • Metitepine/Methiothepin • Nantenine • Pimavanserin • Pizotifen •
Pruvanserin • Rauwolscine • Ritanserin • S-14,671 • Sarpogrelate • Setoperone • Spiperone • Spiramide •
SR-46349B • Volinanserin • Xylamidine • Yohimbine

Agonists: Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: Chlorphentermine • Cloforex • DOB •

DOC • DOI • DOM • Fenfluramine • MDA • MDMA • Norfenfluramine; Tryptamines: 5-CT • 5-MT • α-Methyl-5-HT;
Others: BW-723C86 • Cabergoline • mCPP • Pergolide • PNU-22394 • Ro60-0175
5-HT 2B
Antagonists: Agomelatine • Asenapine • EGIS-7625 • Ketanserin • Lisuride • LY-272,015 •
Metitepine/Methiothepin • PRX-08066 • Rauwolscine • Ritanserin • RS-127,445 • Sarpogrelate • SB-200,646 •
SB-204,741 • SB-206,553 • SB-215,505 • SB-221,284 • SB-228,357 • SDZ SER-082 • Tegaserod • Yohimbine

Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM • MDA •
MDMA • Mescaline; Piperazines: Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET •
5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT •
Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: A-372,159 • AL-38022A • CP-809,101 •
Dimemebfe • Lorcaserin• Medifoxamine • MK-212 • ORG-37,684 • Oxaflozane • PNU-22394 • Ro60-0175 •
Vabicaserin • WAY-629 • WAY-161,503 • YM-348
Antagonists: Atypical antipsychotics: Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide •
5-HT 2C
Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical antipsychotics: Chlorpromazine • Loxapine •
Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Aptazapine • Etoperidone • Fluoxetine •
Mianserin • Mirtazapine • Nefazodone • Nortriptyline • Trazodone; Others: Adatanserin • Cinanserin •
Cyproheptadine • Deramciclane • Dotarizine • Eltoprazine • Esmirtazapine • FR-260,010 • Ketanserin • Ketotifen •
Latrepirdine • Lu AA24530 • Metitepine/Methiothepin • Methysergide • Pizotifen • Ritanserin • RS-102,221 •
S-14,671 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082 •
Xylamidine

  5-HT 3 , 5-HT 4 , 5-HT 5 , 5-HT 6 , 5-HT 7 ligands

Agonists: Piperazines: BZP • Quipazine; Tryptamines: 2-Methyl-5-HT • 5-CT; Others: Chlorophenylbiguanide •

Butanol • Ethanol • Halothane • Isoflurane • RS-56812 • SR-57,227 • SR-57,227-A • Toluene • Trichloroethane •
Trichloroethanol • Trichloroethylene • YM-31636

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Venlafaxine - Wikipedia, the free encyclopedia

Antagonists: Antiemetics: AS-8112 • Alosetron • Azasetron • Batanopride • Bemesetron • Cilansetron • Dazopride •

5-HT 3
Dolasetron • Granisetron • Lerisetron • Ondansetron • Palonosetron • Ramosetron • Renzapride • Tropisetron •
Zacopride • Zatosetron; Atypical antipsychotics: Clozapine • Olanzapine • Quetiapine; Tetracyclic antidepressants:
Amoxapine • Mianserin • Mirtazapine; Others: CSP-2503 • ICS-205,930 • Lu AA21004 • Lu AA24530 •
MDL-72,222 • Memantine • Nitrous Oxide • Ricasetron • Sevoflurane • Thujone  • Xenon

Agonists: Gastroprokinetic Agents: Cinitapride • Cisapride • Dazopride • Metoclopramide • Mosapride •

Prucalopride • Renzapride • Tegaserod • Zacopride; Others: 5-MT • BIMU-8 • CJ-033,466 • PRX-03140 •
5-HT 4
RS-67333 • RS-67506 • SL65.0155 • TD-5108
Antagonists: GR-113,808 • GR-125,487 • L-Lysine • Piboserod • RS-39604 • RS-67532 • SB-203,186

Agonists: Lysergamides: Ergotamine • LSD; Tryptamines: 5-CT; Others: Valerenic Acid

5-HT 5A Antagonists: Asenapine • Latrepirdine • Metitepine/Methiothepin • Ritanserin • SB-699,551
* Note that the 5 -HT5B receptor is not functional in humans.

Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Lisuride • LSD • Mesulergine • Metergoline •

Methysergide; Tryptamines: 2-Methyl-5-HT • 5-BT • 5-CT • 5-MT • Bufotenin • E-6801 • E-6837 • EMD-386,088 •
EMDT • LY-586,713 • N-Methyl-5-HT • Tryptamine; Others: WAY-181,187 • WAY-208,466
Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Doxepin • Mianserin • Nortriptyline;
5-HT 6
Atypical antipsychotics: Aripiprazole • Asenapine • Clozapine • Fluperlapine • Iloperidone • Olanzapine • Tiospirone;
Typical antipsychotics: Chlorpromazine • Loxapine; Others: BGC20-760 • BVT-5182 • BVT-74316 • EGIS-12233 •
GW-742,457 • Ketanserin • Latrepirdine • Lu AE58054 • Metitepine/Methiothepin • MS-245 • PRX-07034 •
Ritanserin • Ro 04-6790 • Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 • SB-742,457

Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT • Bufotenin; Others: 8-OH-DPAT • AS-19 • Bifeprunox •
LP-12 • LP-44 • RU-24,969 • Sarizotan
Antagonists: Lysergamides: 2-Bromo-LSD • Bromocriptine • Dihydroergotamine • Ergotamine • Mesulergine •
Metergoline • Methysergide; Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Imipramine • Maprotiline •
5-HT 7 Mianserin; Atypical antipsychotics: Amisulpride • Aripiprazole • Clozapine • Olanzapine • Risperidone • Sertindole •
Tiospirone • Ziprasidone • Zotepine; Typical antipsychotics: Chlorpromazine • Loxapine; Others: Butaclamol •
EGIS-12233 • Ketanserin • LY-215,840 • Metitepine/Methiothepin • Pimozide • Ritanserin • SB-258,719 •
SB-258,741 • SB-269,970 • SB-656,104 • SB-656,104-A • SB-691,673 • SLV-313 • SLV-314 • Spiperone •
SSR-181,507

  Reuptake inhibitors

Selective serotonin reuptake inhibitors (SSRIs): Alaproclate • Citalopram • Dapoxetine • Desmethylcitalopram •

Desmethylsertraline • Escitalopram • Femoxetine • Fluoxetine • Fluvoxamine • Indalpine • Ifoxetine • Litoxetine •
Lu AA21004 • Lubazodone • Panuramine • Paroxetine • Pirandamine • RTI-353 • Seproxetine • Sertraline •
Vilazodone • Zimelidine; Serotonin-norepinephrine reuptake inhibitors (SNRIs): Bicifadine • Desvenlafaxine •
Duloxetine • Eclanamine • Levomilnacipran • Milnacipran • Sibutramine • Venlafaxine; Serotonin-norepinephrine-
dopamine reuptake inhibitors (SNDRIs): Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 •
SERT NS-2359 • SEP-225,289 • SEP-227,162 • Tesofensine; Tricyclic antidepressants (TCAs): Amitriptyline • Butriptyline •
Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline •
Pipofezine • Protriptyline • Trimipramine; Tetracyclic antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone •
Trazodone; Antihistamines: Brompheniramine • Chlorpheniramine • Diphenhydramine • Mepyramine/Pyrilamine •
Pheniramine • Tripelennamine; Opioids: Meperidine (Pethidine) • Methadone • Propoxyphene; Others: Cocaine •
CP-39,332 • Cyclobenzaprine • Dextromethorphan • Dextrorphan • EXP-561 • Fezolamine • Mesembrine • Nefopam •
PIM-35 • Pridefrine • Roxindole • SB-649,915 • Ziprasidone

VMAT Ibogaine • Reserpine • Tetrabenazine

  Releasing agents

Aminoindanes: 5-IAI • ETAI • MDAI • MDMAI • MMAI • TAI; Aminotetralins: 6-CAT • 8-OH-DPAT • MDAT • MDMAT;
Oxazolines: 4-Methylaminorex • Aminorex • Clominorex • Fluminorex; Phenethylamines (also Amphetamines, Cathinones,
Phentermines, etc): 2-Methyl-MDA • 4-CAB • 4-FA • 4-FMA • 4-HA • 4-MTA • 5-APDB • 5-Methyl-MDA • 6-APDB •
6-Methyl-MDA • Amiflamine • BDB • BOH • Brephedrone • Butylone • Chlorphentermine • Cloforex • Diethylcathinone •
Dimethylcathinone • DMA • DMMA • EBDB • EDMA • Ethylone • Etolorex • Fenfluramine (Dexfenfluramine) • Flephedrone •

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IAP • IMP • Lophophine • MBDB • MDA • MDEA • MDHMA • MDMA • MDMPEA • MDOH • MDPEA • Mephedrone •
Methedrone • Methylone • MMA • MMDA • MMDMA • NAP • Norfenfluramine • pBA • pCA • pIA • PMA • PMEA • PMMA • TAP;
Piperazines: 2C-B-BZP • BZP • MBZP • mCPP • MDBZP • MeOPP • Mepiprazole • pFPP • TFMPP; Tryptamines:
4-Methyl-αET • 4-Methyl-αMT • 5-CT • 5-MeO-αET • 5-MeO-αMT • 5-MT • αET • αMT • DMT • Tryptamine (itself); Others:
Indeloxazine • Tramadol • Viqualine

  Enzyme inhibitors

TPH AGN-2979 • Fenclonine

Anabolism
AAAD Benserazide • Carbidopa • Genistein • Methyldopa

Nonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone • Hydralazine • Indantadol •

Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine •
Nialamide • Octamoxin • Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine •
Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Amiflamine •
Catabolism MAO
Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone •
Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) •
Methylene Blue • Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole •
Toloxatone • Tyrima

  Others

Precursors L-Tryptophan → 5-HTP

Ferrous iron (Fe2+ ) • Magnesium (Mg 2+ ) • Tetrahydrobiopterin • Vitamin B 3 (Niacin, Nicotinamide → NADPH) •
Cofactors Vitamin B 6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal phosphate) • Vitamin B 9 (Folic Acid →
Tetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+ )

Others Activity enhancers: BPAP • PPAP; Reuptake enhancers: Tianeptine

Categories: Alcohols | Bicyclic antidepressants | Drugs | Phenol ethers | Serotonin-norepinephrine-

dopamine reuptake inhibitors

This page was last modified on 11 January 2011 at 04:31.

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http://en.wikipedia.org/wiki/Venlafaxine[1/12/2011 3:46:52 PM]